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John came out of retirement once again in 2016 when he was appointed as player-coach of Central F.C. in the TT Pro League.

John retired and moved back to his native Trinidad and Tobago after his spell at Solihull Moors. He came out of retirement a second time in order to join WASA FC of the National Super League of Trinidad and Tobago in January 2014. He scored on his debut

In August 2012, after two seasons out of English football, John returned, signing for Solihull Moors. However, as of November 2012, he had yet to make an appearance in any competition for the club.

On 29 July 2009 John signed for Crystal Palace on a year-long deal after turning down an offer to stay at Southampton. He made his debut on the opening day of the season against Plymouth Argyle, he had to come off after 35 minutes due to an injury. He returned in mid-October, but joined Ipswich Town on a one-month loan at the end of November. He scored his first goal for Ipswich in a 3–2 win over Coventry City on 16 January 2010. Upon his return to Palace he scored his first goal for the club in a 3–1 win at Watford on 30 March 2010. New Palace manager George Burley had hoped to discuss the player's future at the end of the season, but no discussion occurred, and John left the club.

John was loaned to Bristol City in October 2008 until the end of the 2008–09 season. John made his first Bristol City appearance, coming on as a substitute, against Barnsley in a 0–0 draw. John scored his first goal for Bristol City in a 4–1 defeat to Reading at Ashton Gate Stadium on 1 November 2008.

On 29 January 2007, John was transferred to Sunderland for an undisclosed fee. The signing was Sunderland manager Roy Keane's sixth signing of the 2006–07 season January transfer window. He scored his first goals against Southend United in a 4–0 victory on 17 February 2007.

On 29 August 2007, John moved to Southampton as part of a deal that took his international teammate Kenwyne Jones in the opposite direction.

He scored his first goals with two in a 3–2 win against West Bromwich Albion on 6 October 2007. From then on he scored regularly for "The Saints", with nine goals in his first fifteen appearances, including a second half hat trick against Hull City on 8 December 2007. He finished the 2007–08 season fourth highest scorer in the Championship with 19 goals for Southampton. (He had also scored once for Sunderland in the Premier League prior to his transfer.) Before being sent off for a second bookable offence, John scored two goals, including the match winner, in Southampton's final game of the season against Sheffield United, as the Saints narrowly avoided relegation to League One.

At the start of the 2005–06 season, following the signing of James Scowcroft, John found himself outside of manager Micky Adams's first-team plans. As a result, he was loaned to Derby County on 16 September 2005. He rejoined Coventry three months later.

At Birmingham, John rarely played, although he had some memorable moments in the blue shirt of Birmingham, such as his turn and finish away at West Ham in 2002; his last minute equaliser at Villa Park in the Birmingham derby; and his last minute goal away at Millwall which put Birmingham through to the Playoff Final in 2002. He then scored one of the penalties in the play-off final shootout to help them get promoted to the Premier League. Popular with the Birmingham fans for his crucial and sometimes brilliant goals, he nonetheless fell out of favour with management, and was sold to Coventry City on 14 September 2004.

After the 1999 season with Columbus, John was acquired by Nottingham Forest of the English First Division for a fee of £1.5 million. However, eventual financial difficulties at Forest following the team's failed bid at promotion forced John's sale to Birmingham City in February 2002, then pushing for promotion to the Premier League, for the sum of £100,000. John scored 18 goals in 49 starts for Forest.

John was born in Tunapuna, Trinidad and Tobago and moved to the United States to attend Mercer County Community College in 1995. He joined the Columbus Crew of Major League Soccer (MLS) from the now-defunct New Orleans Riverboat Gamblers of the A-League for the 1998 season. On the recommendation of his older cousin, Columbus Crew defender and Trinidad and Tobago international, Ansil Elcock, John received a try-out with Crew, where he became one of the most prolific scorers in league history. In 1998, John led the league with 26 goals, a record that currently puts him tied for fifth in MLS for goals in one season, and also with 57 points to be named the MLS Scoring Champion. He was named to the MLS Best XI that year as well, and tied for the lead with 18 goals in 1999.

John made his international debut for Trinidad and Tobago national football team on 15 February 1995 against Finland in a Friendly match at the Queen's Park Oval, scoring one goal on his debut. John has been a vital player for the Soca Warriors, currently the team's all-time leading scorer with 70 goals in 115 caps (as of 9 February 2011), and is also the 7th highest international goalscorer according to the list of Top international association football goal scorers by country, behind Pelé, Ferenc Puskás and Ali Daei. He is also the all-time top CONCACAF goal scorer. He was instrumental in helping his country qualify for the 2006 FIFA World Cup and played in all three of his country's World Cup group matches at Germany 2006. In Germany, he scored an offside goal. He was also named Trinidad and Tobago Football Federation Player of the Year in 2002. John is currently the second most capped Trinidad and Tobago international behind former teammate Angus Eve. He was the only player to score in 12 consecutive international matches, from 1998 to 1999.

Stern John, CM (born 30 October 1976) is a Trinidadian football manager and former player who is currently managing Central F.C. in the TT Pro League. He previously played for a number of American and English football clubs that included Columbus Crew, Bristol City, Nottingham Forest, Birmingham City, Sunderland, Southampton, Crystal Palace, Coventry City and Derby County.